Potassium Iodide → HCID 53712448, compound

HRID 892478Notes

Reaction equation

HRID 892478 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[CH:14][O:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11].[CH:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[C:22]([SH:27])[CH:23]=[CH:24]2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.O>[CH:21]1[C:20]2[C:25](=[CH:26][CH:17]=[CH:18][CH:19]=2)[CH:24]=[CH:23][C:22]=1[S:27][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[CH:14][O:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 70582-NaphthalenethiolHCID 11430Potassium CarbonateHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate

Product 1

HCID 53712448HCID 53712448, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

8 g of methyl α-(2-bromomethylphenyl)-β-methoxyacrylate, 4.5 g of 2-thionaphthol, 4.4 g of potassium carbonate and 100 mg of potassium iodide are refluxed for 20 hours in 200 ml of acetone. 200 ml of water is then added and extraction is carried out three times with methylene chloride. The organic phases are dried over Na2SO4 and evaporated down. The oil which remains is chromatographed on silica gel using a mixture of n-hexane and ethyl acetate. There is obtained 8.19 g of slightly yellow crystals of melting point 52°-58° C.

Workup

  1. extractionextraction
  2. dry with materialThe organic phases are dried over Na2SO4
  3. customevaporated down
  4. customThe oil which remains is chromatographed on silica gel using
  5. additiona mixture of n-hexane and ethyl acetate
  6. customThere is obtained 8.19 g of slightly yellow crystals of melting point 52°-58° C.

Sources & evidence

ORD record
ord-693acefa7318475aa99e88988992e5f9
Source dataset
uspto-grants-1992_06
Patent number
US05118710

Reaction notes

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